Production of alkylated phenols



wherein Band B are alkyl or aryl radicals;

sat-ion of a Patented Na. 25, 71930 HANS JORDAN, 0F IBER-LIN-STEGLI'IZ, GER ANY. AssIeNoR TOQCHEMISCHE FA RIK AUF ACTIEH (voiaivi. nscnnnme); OF-IBERLIE GERIYLANY a PRODUCTION or aniiiriiarnn mamas) a "No Drawin Application fiIedJuIy 12, 1926, se ial at. 122,031 an i Germany iin i, lean f My invention refers to theproductioni of alkylated phenols.

formula with hydrogen in the presence of a catalyst 1m .tl tth lo 1e flthecona q a m Sum anner 1a 8 m0 9 u 0 tELII S Of the operation and particularly in densation product is split up at the point where: the ketone connects the two phenolradicals. This'operation is preferably cari tried out by treating the product of condensation with hydrogen in the presence of a catalyst until two hydrogen atoms have Ca: D1

been fixed. t The alkylated phenols obtainable in this manner have the formula u n M R 3" I have further found that a nickel catalyst so as not to cause a further hydrogenation containing bismuth andwhich acts slowly of the jphenols obtained is particularly suitable.

In practicing my invention I prefer proceeding for instance as follows:

Ewamplel 100 parts by weight of p-dihydroxy dican: easily be separatedfromeach other by distillation. p

Example 2 v I l-dihydrdxy-S-dimethyl diphenyl dimethy methane (see Unverzagts dissertation Ueber di Einwir kung vonBrom dimethylmethan, published at Marburg in containing bismuth substantially as described with reference to Example 1. The products obtained are2-methyl-i-isopropyl phenol and Y Various! changes may be made inithe de- 6 theproportions of the ingredients without departing from'the-l invention jor sacrificing the advantages thereof. k I; claim a 1 1, The method iof fproducing y-alkyllated r-i ne om r g ll ie ingad hydr ydiphenyl methane derivative having the formula I, p

Rom O on a c a I are 4 alkyl or; arylfradicals at a temperature;not lmaterially exceeding"? ethyl methane as described with reference to Example 1 there {is phenol an dphenol.

0 5.1609 G-jt r tm nt ithitl ydro nintthe presence; of a slow actinghydrogenation catalyst whereby the molecule of the ,cornpound is splitflup at the point w ereas; can

- If 2- @The methodof producing alkylated phephenyl dimethyl methane are treated at about 160 C. with hydrogen under pressure f in the presence of 1 to 3 parts of a nickel" catalyst containing bismuth, until two hydrogen atoms have been fixed. There isformedp-isopropyl phenoland phenol, which I nols comprising subjecting a dihydroxy-di phenyl methane derivative having the fora i 1 a A wherein R 1 and mula at a temperature not materially exceeding 160 C. to treatment with hydrogen in the wbon atomconneots the two phenol radicals; 3 l

are alkyl or aryl radicals) presence of a slow acting hydrogenation cata lyst until two hydrogen atoms. have been fixed.

3. The method of producing alkylated phenols comprising subjecting a dihydroxydiphenyl methane derivative having the formula no on 00/0 wherein R and R are alkyl or aryl radicals, at a temperature not materially exceeding 160 C. to treatment with hydrogen in the presence of a slow acting mixed hydrogenation catalyst whereby the molecule of the compound is split up at the point Where the carbon atom connects the two phenol radicals.

4:. The method of producing alkylated phenols comprising subjecting a dihydroxydiphenyl methane derivative having the forwherein R and R are alkyl or aryl' radicals, at a temperature not materially exceeding 160 C. to treatment with hydrogen in the presence of a slow acting hydrogenation catalyst containing bismuth whereby the molecule of the compound is split up at the point where the carbon atom connects the two phenol radicals.

5. The method of producing alkylated phenols comprising subjecting a dihydroxy-diphenyl methane derivative having the formula no on V I :\O/: R R

wherein R andrR are alkyl or aryl radicals, at a temperature not materially exceeding 160? C. to treatment with hydrogen in the presence of a nickel catalyst containing bismuth whereby the molecule of the compound is split up at the point where the carbon atomconnects the tWo phenol radicals.

6. The method of producing p-isopropyl phenol comprising treating parts by weight of p-dihydroxy-diphenyl dimethyl methane at about C. With hydrogen under pressure in the presence of l to 3 parts of a nickel catalyst containing bismuth until tWo hydrogen atoms have been fixed, and removing phenol by distillation.

In testimony whereof I aflix my signature.

HANS JORDAN. 

